Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
  • A61K36/16—Ginkgophyta, e.g. Ginkgoaceae (Ginkgo family)
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
  • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
  • A61K8/9771—Ginkgophyta, e.g. Ginkgoaceae [Ginkgo family]
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders

Definitions

• the invention relates to a new extract from the leaves of Ginkgo biloba and its method of preparation.
• Certain extracts from the leaves of Ginkgo biloba are widely used for the therapy of peripheral and cerebral arterial circulatory disturbances.
• Various processes for preparing such extracts are described for example in DE-B -1767098, DE-B2117429, EP-A 0 324 197, EP-A 330 567 and EP-A 0 436 129.
• the invention also provides a method for preparing a glycolipid extract from Ginkgo biloba leaves comprising the steps of:
• the leaves of Ginkgo biloba are first extracted with an organic solvent such as acetone/water and the resulting solution is concentrated, for example, by evaporation and cooled.
• the solution is then filtered and a C 1 -C 3 alcohol such as ethanol is added to the precipitate.
• the solution is agitated and again filtered.
• the filtrate is adjusted with water and extracted with a suitable organic solvent especially a non polar solvent such as heptane.
• a suitable organic solvent especially a non polar solvent such as heptane.
• the particular advantage of extraction with a non polar solvent prior to application to a chromatographic column is that the solvent removes a substantial proportion, typically 30%, of the dry extract. As a result the amount of desired extract, particularly digalactosyldiglycerides, is increased.
• the aqueous alcoholic phase is then evaporated to dryness, or evaporated and filtered and an organic solvent is added.
• the resulting solution is filtered, and then purified by
• the organic solvent in which the concentrated alcoholic solution in dissolved is the same as a first extracting medium applied to the column. This optimises the chromatographic process.
• the concentrated alcoholic solution from which neutral lipids have been removed is treated with at least two different extracting media.
• the advantage of this feature is in facilitating the targeted extraction of a desired fraction from the material applied to the column.
• the acetone/toluene is preferably 5 to 30%, especially approximately 20%.
• One of the extracting media may be acetone which is again a useful solvent for target extracts.
• a desired fraction obtained by extraction is concentrated, redissolved and reprocessed through the chromatographic column to produce a more concentrated desired fraction.
• the medium containing the desired fraction is purified by treating with charcoal and filtering the desired extract to remove the charcoal.
• the extract was separated from the leaves and was then concentrated by evaporation.
• the concentrate was cooled to 8°-10° C. and was retained at this temperature for 3 hours.
• the lipids which precipitated were recovered by decanting.
• the recovered lipids were then dissolved in an agitated solution of 2.9 kg of acetone and 0.7 kg of demineralised water. A further 30 kg of demineralised water was then added.
• the solution was continuously agitated and cooled to 8°-10° C. and was retained for a minimum of 3 hours before being decanted.
• the wet decanted lipids from Step 2 were added to 80 kg of ethanol and agitated for 3 hours.
• the ethanolic solution from Step 3 was adjusted to 12-15% water.
• the ethanol-water phase was evaporated to greater than 85% dry extract.
• the alcoholic solution containing the extract from Step 4 was dissolved in 40% acetone/toluene and retained at ambient temperature overnight.
• This solution was filtered and was then applied to 18 kg of silica in a packed column.
• the following solvents were pumped through the column: -200 l 20% acetone/toluene, 400 l 40% acetone/toluene, 100 l acetone and 120 l 8% ethanol/acetone.
• the desired fraction extracted by the third extraction medium (acetone) applied to the column was evaporated and redissolved in 40% acetone/toluene and reprocessed through the column using the same conditions as above and three main fractions taken.
• the first peak was characteristic of mono-galactosyldiglycerides.
• the third peak was characteristic of digalactosyldiglycerides which are the preferred extract.
• the peaks eluting between the mono and digalactosyldiglycerides may be cerebroside in character.
• the second of the three fractions obtained in Step 6 above contains greater than 70 to 80% of the material corresponding to the second major peak. This fraction may be cerebroside in character.
• the concentrate was cooled to 8°-10° C. and was retained at this temperature for 3 hours.
• the lipids which precipitated were recovered by decanting.
• the solution was continuously agitated and cooled to 8°-10° C. and was retained for a minimum of 3 hours before being decanted.
• the wet decanted lipids from Step 2 were added to 34 kg of ethanol and agitated for 3 hours.
• the extract from Step 4 was dissolved in 80% acetone/toluene and retained at ambient temperature overnight.
• the glyceride moiety of the digalactosyldiglycerides was identified by hydrolysis and gas chromatography analysis of the methyl esters.
• the lipids which precipitated were recovered by decanting.
• the recovered lipids were then dissolved in an agitated solution of 2.9 kg of acetone and 0.7 kg of demineralised water. A further 30 kg of demineralised water was then added.
• the solution was continuously agitated and cooled to 8°-10° C. and was retained for a minimum of 3 hours before being decanted.
• the wet decanted lipids from Step 2 were added to 80 kg of ethanol and agitated for 3 hours.
• the ethanolic solution from Step 3 was adjusted to 12-15% water.
• the precipitate from Step 4 was dissolved in 50% acetone/toluene and retained at ambient temperature overnight.
• This solution was filtered and was then applied to 18 kg of silica in a packed column.
• the following solvent was pumped through the column:- 180 l 50% acetone/toluene, and 120 l 8% ethanol/acetone.
• the ethanol/acetone fraction was evaporated and redissolved in 70% acetone/toluene and reprocessed through the column.
• the digalactosyldiglyceride and cerebroside extracts have shown activity in cosmetic and skin care applications.

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• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Natural Medicines & Medicinal Plants (AREA)
• Veterinary Medicine (AREA)
• Public Health (AREA)
• General Health & Medical Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• Engineering & Computer Science (AREA)
• Microbiology (AREA)
• Botany (AREA)
• Epidemiology (AREA)
• Mycology (AREA)
• Biotechnology (AREA)
• Pharmacology & Pharmacy (AREA)
• Medicinal Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Medical Informatics (AREA)
• Dermatology (AREA)
• Alternative & Traditional Medicine (AREA)
• Birds (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Bioinformatics & Cheminformatics (AREA)
• General Chemical & Material Sciences (AREA)
• Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
• Organic Chemistry (AREA)
• Medicines Containing Plant Substances (AREA)
• Saccharide Compounds (AREA)
• Cosmetics (AREA)
• Steroid Compounds (AREA)

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Citations (9)

• 1996
  • 1996-05-31 WO PCT/IE1996/000034 patent/WO1996038160A1/fr active IP Right Grant
  • 1996-05-31 EP EP96916282A patent/EP0828501B1/fr not_active Expired - Lifetime
  • 1996-05-31 IE IE960402A patent/IE960402A1/en not_active IP Right Cessation
  • 1996-05-31 AT AT96916282T patent/ATE277626T1/de not_active IP Right Cessation
  • 1996-05-31 DE DE69633507T patent/DE69633507D1/de not_active Expired - Lifetime
  • 1996-05-31 CN CN96194311A patent/CN1186437A/zh active Pending
  • 1996-05-31 AU AU59091/96A patent/AU5909196A/en not_active Abandoned
  • 1996-05-31 KR KR1019970708421A patent/KR100431376B1/ko not_active IP Right Cessation
  • 1996-05-31 JP JP8536348A patent/JPH11506095A/ja not_active Ceased
  • 1996-05-31 US US08/952,893 patent/US5885582A/en not_active Expired - Fee Related

Patent Citations (9)

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